Self-assembly and antimicrobial activity of long-chain amide-functionalized ionic liquids in aqueous solution

Colloids and Surfaces B: Biointerfaces

Volumn 123, Issue , 2014, Pages 318-325

  Garcia, M Teresa ^a   Ribosa, Isabel ^a   Perez, Lourdes ^a   Manresa, Angeles ^b   Comelles, Francesc ^a  

^a INSTITUTE OF ADVANCED CHEMISTRY OF CATALONIA IQAC CSIC   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Aggregation behaviour; Antimicrobial activity; Functionalized ionic liquids; Surface activity

Indexed keywords

AGGLOMERATION; AMIDES; ANTIMICROBIAL AGENTS; BACTERIA; CRITICAL MICELLE CONCENTRATION; FUNCTIONAL GROUPS; HYDROPHOBICITY; SELF ASSEMBLY; SOLUTIONS; THERMODYNAMIC STABILITY;

AGGREGATION BEHAVIOURS; ANTI-BACTERIAL ACTIVITY; ANTI-MICROBIAL ACTIVITY; AQUEOUS SOLUTION OF AMIDES; CRITICAL MICELLE CONCENTRATION (CMC); FUNCTIONALIZED IONIC LIQUIDS; GRAM-POSITIVE BACTERIUM; SURFACE ACTIVITIES;

IONIC LIQUIDS;

AMIDE; ESTER DERIVATIVE; IMIDAZOLE DERIVATIVE; IONIC LIQUID; PYRIDINIUM DERIVATIVE; SURFACTANT;

ADSORPTION KINETICS; ANTIMICROBIAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CHEMICAL MODIFICATION; CONCENTRATION (PARAMETERS); CONDUCTANCE; CONTROLLED STUDY; FUNGUS; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HYDROGEN BOND; HYDROPHOBICITY; MICELLIZATION; NONHUMAN; SPECTROFLUOROMETRY; SURFACE PROPERTY; THERMOSTABILITY;

EID: 84915751633     PISSN: 09277765     EISSN: 18734367     Source Type: Journal    
DOI: 10.1016/j.colsurfb.2014.09.033     Document Type: Article

References (56)

1. Plechkova N.V., Seddon K.R. Applications of ionic liquids in the chemical industry. Chem. Soc. Rev. 2008, 37:123-150. 10.1039/b006677j.
2. van Rantwijk F., Sheldon R.A. Biocatalysis in ionic liquids. Chem. Rev. 2007, 107:2757-2785. 10.1021/cr050946x.
3. Olivier-Bourbigou H., Magna L., Morvan D. Ionic liquids and catalysis: recent progress from knowledge to applications. Appl. Catal. Gen. 2010, 373:1-56. 10.1016/j.apcata.2009.10.008.
4. Poole C.F., Poole S.K. Extraction of organic compounds with room temperature ionic liquids. J. Chromatogr. A 2010, 1217:2268-2286. 10.1016/j.chroma.2009.09.011.
5. Torimoto T., Tsuda T., Okazaki K., Kuwabata S. New frontiers in materials science opened by ionic liquids. Adv. Mater. 2010, 22:1196-1221. 10.1002/adma.200902184.
6. Dupont J., Scholten J.D. On the structural and surface properties of transition-metal nanoparticles in ionic liquids. Chem. Soc. Rev. 2010, 39:1780-1804. 10.1039/b822551f.
7. Garcia M.T., Gathergood N., Scammells P. Biodegradable ionic liquids - part II. Effect of the anion and toxicology. Green Chem. 2005, 7:9-14. 10.1039/b411922c.
8. Morrissey S., Pegot B., Coleman D., Garcia M.T., Ferguson D., Quilty B., Gathergood N. Biodegradable, non-bactericidal oxygen-functionalised imidazolium esters: a step towards greener ionic liquids. Green Chem. 2009, 11:475-483.
9. Lee S.G. Functionalized imidazolium salts for task-specific ionic liquids and their applications. Chem. Commun. 2006, 104:9-1063. 10.1039/b514140k.
10. Zhao H., Jones C.L., Cowins J.V. Lipase dissolution and stabilization in ether-functionalized ionic liquids. Green Chem. 2009, 11:1128-1138. 10.1039/b905388c.
11. Li H., Li Z., Yin J., Li C., Chi Y., Liu Q. Liquid-liquid extraction process of amino acids by a new amide-based functionalized ionic liquid. Green Chem. 2012, 14:1721-1727. 10.1039/c2gc16560k.
12. Bowers J., Butts C.P., Martin P.J., Vergara-Gutierrez M.C., Heenan R.K. Aggregation behavior of aqueous solutions of ionic liquids. Langmuir 2004, 20:2191-2198. 10.1021/la035940m.
13. Dong B., Li N., Zheng L.Q., Yu L., Inoue T. Surface adsorption and micelle formation of surface active ionic liquids in aqueous solution. Langmuir 2007, 23:4178-4182. 10.1021/la0633029.
14. Jungnickel C., Luczak J., Ranke J., Fernandez J.F., Muller A., Thoming J. Micelle formation of imidazolium ionic liquids in aqueous solution. Colloids Surf. Physicochem. Eng. Asp. 2008, 316:278-284. 10.1016/j.colsurfa.2007.09.020.
15. Blesic M., Lopes A., Melo E., Petrovski Z., Plechkova N.V., Lopes J.N.C. On the self-aggregation and fluorescence quenching aptitude of surfactant ionic liquids. J. Phys. Chem. B 2008, 112:8645-8650. 10.1021/jp802179j.
16. Cornellas A., Perez L., Comelles F., Ribosa I., Manresa A., Garcia M.T. Self-aggregation and antimicrobial activity of imidazolium- and pyridinium-based ionic liquids in aqueous solution. J. Colloid Interface Sci. 2011, 355:164-171. 10.1016/j.jcis.2010.11.063.
17. Luczak J., Hupka J., Thoming J., Jungnickel C. Self-organization of imidazolium ionic liquids in aqueous solution. Colloids Surf. Physicochem. Eng. Asp. 2008, 329:125-133. 10.1016/j.colsurfa.2008.07.012.
18. Wang X.Q., Yu L., Jiao J.J., Zhang H.N., Wang R., Chen H. Aggregation behavior of COOH-functionalized imidazolium-based surface active ionic liquids in aqueous solution. J. Mol. Liq. 2012, 173:103-107. 10.1016/j.molliq.2012.06.023.
19. Chauhan V., Singh S., Bhadani A. Synthesis, characterization and surface properties of long chain beta-hydroxy-gamma-alkyloxy-N-methylimidazolium surfactants. Colloids Surf. Physicochem. Eng. Asp. 2012, 395:1-9. 10.1016/j.colsurfa.2011.11.022.
20. Garcia M.T., Ribosa I., Perez L., Manresa A., Comelles F. Aggregation behavior and antimicrobial activity of ester-functionalized imidazolium- and pyridinium-based ionic liquids in aqueous solution. Langmuir 2013, 29:2536-2545.
21. Pernak J., Sobaszkiewicz K., Mirska I. Anti-microbial activities of ionic liquids. Green Chem. 2003, 5:52-56. 10.1039/b207543c.
22. Garcia M.T., Gathergood N., Scammells P.J. Biodegradable ionic liquids - part II. Effect of the anion and toxicology. Green Chem. 2005, 7:9-14.
23. Ranke J., Molter K., Stock F., Bottin-Weber U., Poczobutt J., Hoffmann J. Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays. Ecotoxicol. Environ. Saf. 2005, 60:350. (vol. 58, p. 396, 2004).
24. Morrissey S., Pegot B., Coleman D., Garcia M.T., Ferguson D., Quilty B., Gathergood N. Biodegradable, non-bactericidal oxygen-functionalised imidazolium esters: a step towards greener ionic liquids. Green Chem. 2009, 11:475-483. 10.1039/b812809j.
25. Gathergood N., Garcia M.T., Scammells P. Biodegradable ionic liquids: part I. Concept, preliminary targets and evaluation. Green Chem. 2004, 6:166-175. 10.1039/b315270g.
26. Kanjilal S., Sunitha S., Reddy P.S., Kumar K.P., Murty U.S.N., Prasad R.B.N. Synthesis and evaluation of micellar properties and antimicrobial activities of imidazole-based surfactants. Eur. J. Lipid Sci. Technol. 2009, 111:941-948. 10.1002/ejlt.200800292.
27. Dong B., Zhao X.Y., Zheng L.Q., Zhang J., Li N., Inoue T. Aggregation behavior of long-chain imidazolium ionic liquids in aqueous solution: micellization and characterization of micelle microenvironment. Colloids Surf. Physicochem. Eng. Asp. 2008, 317:666-672. 10.1016/j.colsurfa.2007.12.001.
28. Kalyanasundaram K., Thomas J.K. Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J. Am. Chem. Soc. 1977, 99:2039-2044.
29. Jones R.N., Barry A.L., Gavan T.L. Manual of Clinical Microbiology 1985, American Society for Microbiology, Washington, DC. 4th ed.
30. Fredlake C.P., Crosthwaite J.M., Hert D.G., Aki S., Brennecke J.F. Thermophysical properties of imidazolium-based ionic liquids. J. Chem. Eng. Data 2004, 49:954-964. 10.1021/je034261a.
31. Arellano I.H.J., Guarino J.G., Paredes F.U., Arco S.D. Thermal stability and moisture uptake of 1-alkyl-3-methylimidazolium bromide. J. Therm. Anal. Calorim. 2011, 103. 10.1007/s10973-010-0992-5.
32. Huddleston J.G., Visser A.E., Reichert W.M., Willauer H.D., Broker G.A., Rogers R.D. Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chem. 2001, 3:156-164.
33. Aggarwal R., Singh S., Hundal G. Synthesis, characterization, and evaluation of surface properties of cyclohexanoxycarbonylmethylpyridinium and cyclohexanoxycarbonylmethylimidazolium ionic liquids. Ind. Eng. Chem. Res. 2013, 52:1179-1189. 10.1021/ie3020473.
34. Vanyur R., Biczok L., Miskolczy Z. Micelle formation of 1-alkyl-3-methylimidazolium bromide ionic liquids in aqueous solution. Colloids Surf. Physicochem. Eng. Asp. 2007, 299:256-261. 10.1016/j.colsurfa.2006.11.049.
35. Hoffmann H., Ulbricht W. Kinetic and thermodynamic measurements on aggregation of perfluorinated surfactants. Z. Phys. Chem. Frankf. 1977, 106:167-184.
36. Blesic M., Marques M.H., Plechkova N.V., Seddon K.R., Rebelo L.P.N., Lopes A. Self-aggregation of ionic liquids: micelle formation in aqueous solution. Green Chem. 2007, 9:481-490. 10.1039/b615406a.
37. Sastry N.V., Vaghela N.M., Macwan P.M., Soni S.S., Aswal V.K., Gibaud A. Aggregation behavior of pyridinium-based ionic liquids in water - surface tension, H-1 NMR chemical shifts, SANS and SAXS measurements. J. Colloid Interface Sci. 2012, 371:52-61. 10.1016/j.jcis.2011.12.077.
38. Garcia M.T., Campos E., Dalmau M., Ribosa I., Sanchez-Leal J. Structure-activity relationships for association of linear alkylbenzene sulfonates with activated sludge. Chemosphere 2002, 49:279-286. 10.1016/S0045-6535(02)00182-0.
39. Rosen M.J. Surfactants and Interfacial Phenomena 2004, Wiley Interscience, New York. 3rd ed.
40. Shimizu S., El Seoud O.A. Synthesis and aggregation of benzyl(2-acylaminoethyl)dimethylammonium chloride surfactants. Langmuir 2003, 19:238-243. 10.1021/la026286y.
41. Klevens H.B. Structure and aggregation in dilute solutions of surface active agents. J. Am. Oil Chem. Soc. 1953, 30:74-80. 10.1007/bf02635002.
42. Baltazar Q.Q., Chandawalla J., Sawyer K., Anderson J.L. Interfacial and micellar properties of imidazolium-based monocationic and dicationic ionic liquids. Colloids Surf. Physicochem. Eng. Asp. 2007, 302:150-156. 10.1016/j.colsurfa.2007.02.012.
43. El Seoud O.A., Pires P.A.R., Abdel-Moghny T., Bastos E.L. Synthesis and micellar properties of surface-active ionic liquids: 1-alkyl-3-methylimidazolium chlorides. J. Colloid Interface Sci. 2007, 313:296-304. 10.1016/j.jcis.2007.04.028.
44. Shi L.J., Li N., Yan H., Gao Y.A., Zheng L.Q. Aggregation behavior of long-chain N-aryl imidazolium bromide in aqueous solution. Langmuir 2011, 27:1618-1625. 10.1021/la104719v.
45. Hiemenz.P.C., Rajagopalan R. Principles of Colloid and Surface Chemistry 1997, Marcel Dekker Inc., New York.
46. Goodchild I., Collier L., Millar S.L., Prokes I., Lord J.C.D., Butts C.P. Structural studies of the phase, aggregation and surface behaviour of 1-alkyl-3-methylimidazolium halide plus water mixtures. J. Colloid Interface Sci. 2007, 307:455-468. 10.1016/j.jcis.2006.11.034.
47. Modaressi A., Sifaoui H., Mielcarz M., Domanska U., Rogalski M. Influence of the molecular structure on the aggregation of imidazolium ionic liquids in aqueous solutions. Colloids Surf. Physicochem. Eng. Asp. 2007, 302:181-185. 10.1016/j.colsurfa.2007.02.020.
48. Sastry N.V., Vaghela N.M., Aswal V.K. Effect of alkyl chain length and head group on surface active and aggregation behavior of ionic liquids in water. Fluid Phase Equilib. 2012, 327:22-29. 10.1016/j.fluid.2012.04.013.
49. Kopecky F. Micellization and other associations of amphiphilic antimicrobial quaternary ammonium salts in aqueous solutions. Pharmazie 1996, 51:135-144.
50. Perez L., Pinazo A., Garcia M.T., Lozano M., Manresa A., Angelet M., Infante M.R. Cationic surfactants from lysine: synthesis, micellization and biological evaluation. Eur. J. Med. Chem. 2009, 44:1884-1892. 10.1016/j.ejmech.2008.11.003.
51. Perez L., Pinazo A., Garcia M.T., Moran M.C., Infante M.R. Monoglyceride surfactants from arginine: synthesis and biological properties. New J. Chem. 2004, 28:1326-1334. 10.1039/b405733c.
52. Carson L., Chau P.K.W., Earle M.J., Gilea M.A., Gilmore B.F., Gorman S.P. Antibiofilm activities of 1-alkyl-3-methylimidazolium chloride ionic liquids. Green Chem. 2009, 11:492-497. 10.1039/b821842k.
53. Franklin T.J., Snow G.A. Biochemistry of antimicrobial action 1989, Chapman and Hall, London. 4th ed.
54. Demberelnyamba D., Kim K.S., Choi S.J., Park S.Y., Lee H., Kim C.J. Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts. Bioorg. Med. Chem. 2004, 12:853-857. 10.1016/j.bmc.2004.01.003.
55. Riduan S.N., Zhang Y. Imidazolium salts and their polymeric materials for biological applications. Chem. Soc. Rev. 2013, 42:9055-9070. 10.1039/c3cs60169b.
56. Luczak J., Jungnickel C., Lacka I., Stolle S., Hupka J. Antimicrobial and surface activity of 1-alkyl-3-methylimidazolium derivatives. Green Chem. 2010, 12:593-601. 10.1039/b921805j.